Ethylamine → HCID 67223854, compound

HRID 1947629Notes

Reaction equation

HRID 1947629 reaction equation
CO[C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[CH2:13]Br.[CH2:16]([NH2:18])[CH3:17]>>[CH2:16]([N:18]1[CH2:13][C:5]2[C:4](=[CH:9][CH:8]=[C:7]([N+:10]([O-:12])=[O:11])[CH:6]=2)[C:3]1=[O:15])[CH3:17]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 15088701Methyl 2-(bromomethyl)-4-nitrobenzoate

Product 1

HCID 67223854HCID 67223854, compoundYield 85%

Procedure

2-Bromomethyl-4-nitro-benzoic acid methyl ester (1.0 g, 3.64 mmol) was stirred in ethylamine (30 ml, 2.0M solution in THF) at room temperature. The reaction was stirred for 3 hrs, after which time the solvent was evaporated in vacuo and the crude residue triturated with diethyl ether. The resulting orange solid was filtered and dried in a vacuum oven (40° C.) to afford the title compound (634 mg, 85%). HPLC retention time 3.56 min. Mass spectrum (ES+) m/z 207 (M+H).

Workup

  1. customafter which time the solvent was evaporated in vacuo
  2. customthe crude residue triturated with diethyl ether
  3. filtrationThe resulting orange solid was filtered
  4. customdried in a vacuum oven (40° C.)

Sources & evidence

ORD record
ord-5ad813b72e9c4db48b1d82d0f7da6752
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

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